Amino silane-based compound, method of preparing the same, and modified conjugated diene-based polymer including the compound

1. An amino silane-based compound represented by Formula 1:

wherein, in Formula 1,

R 1 and R 2 are each independently a glycol unit represented by

R 3 is a divalent hydrocarbon group having 1 to 30 carbon atoms,

R 4 , R 5 , R 6 , and R 7 are each independently a monovalent hydrocarbon group having 1 to 30 carbon atoms,

R 8 is a divalent hydrocarbon group having 1 to 10 carbon atoms,

j and k are each independently 0 or 1,

n is an integer selected from 2 to 10,

wherein i is 1 or 2, and l is 0 or 1.

2. The amino silane-based compound of claim 1 , wherein in Formula 1,

R 3 is an alkylene group having 1 to 10 carbon atoms,

R 4 , R 5 , R 6 , and R 7 are each independently an alkyl group having 1 to 10 carbon atoms,

R 8 is an alkylene group having 1 to 5 carbon atoms,

n is an integer selected from 2 to 8.

3. The amino silane-based compound of claim 1 , wherein the amino silane-based compound represented by Formula 1 is a compound represented by Formula 1-1:

wherein, in Formula 1-1,

R 1 is a glycol unit represented by

R 4 , R 5 , R 6 , and R 7 are each independently a monovalent hydrocarbon group having 1 to 30 carbon atoms,

R 8 is a divalent hydrocarbon group having 1 to 10 carbon atoms,

j and k are each independently 0 or 1, and

n is an integer selected from 2 to 10.

4. The amino silane-based compound of claim 1 , wherein the amino silane-based compound represented by Formula 1 is a compound represented by Formula 1-2:

wherein, in Formula 1-2,

R 1 and R 2 are each independently a glycol unit represented by

R 4 , R 5 , R 6 , and R 7 are each independently a monovalent hydrocarbon group having 1 to 30 carbon atoms,

R 8 is a divalent hydrocarbon group having 1 to 10 carbon atoms,

j and k are each independently 0 or 1, and

n is an integer selected from 1 to 10.

5. A method of preparing an amino silane-based compound of claim 1 , comprising:

reacting a compound represented by Formula 2 with a compound represented by Formula 3 in a polar solvent:

wherein, in Formulae 2 and 3,

R 3 is a divalent hydrocarbon group having 1 to 30 carbon atoms,

R 4 , R 5 , R 6 , R 7 , and R 9 are each independently a monovalent hydrocarbon group having 1 to 30 carbon atoms,

R 8 is a divalent hydrocarbon group having 1 to 10 carbon atoms,

i is 1 or 2,

j and k are each independently 0 or 1, m is 0,

n is an integer selected from 1 to 10, and

X is a leaving group selected from the group consisting of a mesylate group, a tosylate group, and triflate group.

6. The method of claim 5 , wherein a molar ratio of the compound represented by Formula 2 to the compound represented by Formula 3 is in a range of 1:1 to 1:5.

7. The method of claim 5 , wherein the reacting step is performed at a reaction temperature of 10° C. to 100° C.

8. The method of claim 5 , wherein the reacting step further comprises:

reacting the compound represented by Formula 2 with the compound represented by Formula 3 in the presence a polar additive in the polar solvent.

9. The method of claim 8 , wherein the polar additive is an inorganic material or an organic material,

wherein the inorganic material comprises a hydride containing an alkali metal or alkaline earth metal, a hydroxide containing an alkali metal or alkaline earth metal, a carbonate containing an alkali metal or alkaline earth metal, or a mixture thereof, and

the organic material comprises an amine-based base, an alkoxy-based base, or a mixture thereof.

10. A modified conjugated diene-based polymer, comprising:

a conjugated diene-based monomer-derived repeating unit; and

the amino silane-based compound of claim 1 as a function group at one end of the polymer.

11. The modified conjugated diene-based polymer of claim 10 , further comprising an aromatic vinyl monomer-derived repeating unit.

12. The modified conjugated diene-based polymer of claim 10 , wherein the modified conjugated diene-based polymer has a number-average molecular weight (Mn) of 10,000 g/mol to 2,000,000 g/mol.

13. The modified conjugated diene-based polymer of claim 10 , wherein the modified conjugated diene-based polymer has a molecular weight distribution (Mw/Mn) of 1.0 to 5.0.

14. A method of preparing a modified conjugated diene-based polymer, the method comprising:

polymerizing a conjugated diene-based monomer, or an aromatic vinyl-based monomer and the conjugated diene-based monomer, in a hydrocarbon solvent including an organometallic compound to prepare an active polymer coupled with an organometal; and

reacting the active polymer coupled with the organometal with an amino silane-based compound represented by Formula 1:

wherein, in Formula 1,

R 1 and R 2 are each independently a hydrocarbon group having 1 to 30 carbon atoms, or a glycol unit represented by

R 3 is a divalent hydrocarbon group having 1 to 30 carbon atoms,

R 4 , R 5 , R 6 , and R 7 are each independently a monovalent hydrocarbon group having 1 to 30 carbon atoms,

R 8 is a divalent hydrocarbon group having 1 to 10 carbon atoms,

j and k are each independently 0 or 1,

n is an integer selected from 1 to 10,

at least one of R 1 and R 2 is a glycol unit represented by

i is 1 or 2, l is 0 or 1, and 3-i-l is 1 or 2 when R 1 is a glycol unit represented by

i and l are each independently 1 or 2, but are not 2 at the same time, and 3-i-l is 0 or 1 when R 2 is a glycol unit represented by

and

i is 1 or 2, l is 0 or 1, and 3-i-l is 0 or 1 when both R 1 and R 2 are glycol units represented by

15. The method of claim 14 , wherein the organometallic compound is used in an amount of 0.01 mmol to 10 mmol based on total 100 g of the monomer(s).

16. The method of claim 14 , wherein the organometallic compound comprises at least one selected from the group consisting of methyllithium, ethyllithium, propyllithium, n-butyllithium, s-butyllithium, t-butyllithium, hexyllithium, n-decyllithium, t-octyllithium, phenyllithium, 1-naphthyllithium, n-eicosyllithium, 4-butylphenyllithium, 4-tolyllithium, cyclohexyllithium, 3,5-di-n-heptylcyclohexyllithium, 4-cyclopentyllithium, naphtylsodium, naphtylpotassium, lithium alkoxide, sodium alkoxide, potassium alkoxide, lithium sulfonate, sodium sulfonate, potassium sulfonate, lithium amide, sodium amide, potassium amide, and lithium isopropylamide.

17. The method of claim 14 , wherein the hydrocarbon solvent further includes a polar additive.

18. The method of claim 17 , wherein the polar additive comprises at least one selected from the group consisting of tetrahydrofuran, ditetrahydrofurylpropane, diethylether, cycloamylether, dipropyl ether, ethylene dimethyl ether, diethyl glycol, dimethyl ether, tertiary butoxyethoxyethane, bis(3-dimethylaminoethyl)ether, (dimethylaminoethyl)ethylether, trimethylamine, triethylamine, tripropylamine, and tetramethylethylenediamine.

19. The amino silane-based compound selected from the group consisting of N,N-bis(3-(triethoxysilyl)propyl)-2,5,8,11,14-pentaoxyhexadecan-16-amine, N,N-bis(3-(diethoxy(methyl)silyl)propyl)-2,5,8,11,14-pentaoxyhexadecan-16-amine, N,N-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-3-(triethoxysilyl)propan-1-amine, N,N-bis(2-(2-(2-butoxyethoxy)ethoxy)ethyl)-3-(triethoxysilyl)propan-1-amine, N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-3-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl)propan-1-amine, N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N-(3-(trimethyoxysilyl)propyl)butan-1-amine, N-(3,6,9,12-tetraoxahexadecyl)-N-(3-(triethoxysilyl)propyl)-3,6,9,12-tetraoxahexadecan-1-amine, N-(3,6,9,12,15-pentaoxanonandecyl)-N-(3-(triethoxysilyl)propyl)-3,6,9,12,15-pentaoxanonandecan-1-amine, and N,N-bis(3-(triethoxysilyl)propyl)-3,6,9,12,15,18-hexaoxodocosan-1-amine.